The present invention relates to novel pyrimidine derivatives and herbicides containing them as active ingredients.
Pyrimidine derivatives are known, for example, by the specification of international application WO95/12582, the specification of international application WO96/22980 and the specification of international application WO97/12877. However, the pyrimidine derivatives of the present invention have not been known.
A herbicide to be used for crop plants is desired to be a chemical which exhibits a sufficient herbicidal effect at a low dose and yet provides selectivity between crop plants and weeds, when applied to an upland field or to a paddy field. Accordingly, it is an object of the present invention to provide a compound which has an excellent herbicidal activity and selectivity between crop plants and weeds.
Under these circumstances, the present inventors have synthesized various substituted pyrimidine derivatives and have studied their physiological activities. As a result, it has been found that novel substituted pyrimidine derivatives as the compounds of the present invention have excellent herbicidal activities and selectivity between crop plants and weeds, and the present invention has been accomplished. Namely, the present invention provides a pyrimidine derivative represented by the formula (I) 
wherein R1 is a hydrogen atom (except for a case where R2=hydrogen atom, and Wxe2x95x90SO2), a halogen atom, a C1-C6 alkyl group, a C1-C6 alkylcarbonyl C1-C6 alkyl group, a hydroxyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group (this group may be substituted by a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C1-C4 haloalkyl group), a C1-C4 haloalkyl group, a C1-C6 alkoxy group, a C1-C4 haloalkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C3-C6 cycloalkyloxy group, a phenyl group (this group may be substituted by a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C4 haloalkyl group, a C1-C4 haloalkoxy group, a cyano group, a cyano C1-C6 alkyl group, a nitro group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group or a C1-C6 alkylsulfonyl group), a C1-C6 alkylthio group (except for a case where R2=phenyl group, and Wxe2x95x90SO2), a C2-C6 alkenylthio group, a C2-C6 alkynylthio group, a C3-C6 cycloalkylthio group, a C1-C6 alkylsulfinyl group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkynylsulfinyl group, a C3-C6 cycloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfonyl group, a C3-C6 cycloalkylsulfonyl group, a C1-C6 hydroxyalkyl group, a C2-C7 acyl group, a C1-C6 alkoxy C1-C6 alkyl group, a cyano group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkoxycarbonyl C1-C6 alkyl group, a C1-C6 alkoxycarbonyl C2-C6 alkenyl group, a carboxyl group, a carboxyl C1-C6 alkyl group, a di C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkoxyimino C1-C6 alkyl group, a hydroxyimino C1-C6 alkyl group, a dioxolanyl group (this group may be substituted by a C1-C6 alkyl group), an aldehyde group, an oxiranyl group, a NR9R10 group or a CONR9R10 group, R9 is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C4 haloalkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C7 acyl group or a C1-C6 alkylsulfonyl group, R10 is a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C4 haloalkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C7 acyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkoxycarbonyl group or a benzyloxycarbonyl group, here R9 and R10 may, together with the carbon atom to which they are bonded, form a 5- to 7-membered saturated ring, R2 is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkylthio group, a C1-C4 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C3-C6 cycloalkyl group (this group may be substituted by a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C1-C4 haloalkyl group), a C2-C7 acyl group, a cyano group, a di C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkoxyimino C1-C6 alkyl group, a hydroxyimino C1-C6 alkyl group, a dioxolanyl group (this group may be substituted by a C1-C6 alkyl group), a cyano C1-C6 alkyl group, a C1-C6 hydroxyalkyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkoxycarbonyl C1-C6 alkyl group, a CR11R12NR9R10 group, a CONR9R10 group, a CR11R12CONR9R10 group or a group represented by any one of the formulae R2-1 to R2-13: 
(wherein X is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkoxy group, a C1-C6 alkoxy C1-C6 alkyl group, a NR9R10 group, a CONR9R10 group, a C1-C4 haloalkoxy group, a C2-C6 alkenyloxy group, a C3-C6 cycloalkyloxy group, a s C2-C7 acyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsufonyl group, a cyano group, a nitro group or a C1-C4 haloalkyl group, n is an integer of from 1 to 3, when n is an integer of 2 or 3, the plurality of X may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C1-C3 alkylenedioxy group), each of R11 and R12 is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group or a C1-C6 alkoxy group, R3 is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkoxy group, a di C1-C6 alkylamino group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a cyano C1-C6 alkyl group, a C3-C6 cycloalkyl C1-C6 alkyl group, an oxiranyl C1-C6 alkyl group or a C1-C6 alkoxycarbonyl C1-C6 alkyl group, W is a xe2x80x94C(xe2x95x90Q)Zxe2x80x94 group or a xe2x80x94SO2xe2x80x94 group, Q is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, a xe2x80x94NR6xe2x80x94 group, a xe2x80x94CH2CH2xe2x80x94 group, a xe2x80x94CHxe2x95x90CHxe2x80x94 group, a xe2x80x94C(R4)R5xe2x80x94 group, a xe2x80x94C(R4)R5xe2x80x94Qxe2x80x94 group, a xe2x80x94Qxe2x80x94C(R4)R5xe2x80x94 group, a xe2x80x94C(xe2x95x90Q)xe2x80x94 group, a xe2x80x94NR6NR6axe2x80x94 group or a xe2x80x94NR6C(R4)R5xe2x80x94 group, each of R4 and R5 is a hydrogen atom, a C1-C6 alkyl group, a halogen atom, a C1-C6 alkoxy group or a C1-C6 alkylthio group, each of R6 and R6a is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group or a C2-C6 alkynyl group, here R3 and R6 may, together with the carbon atom to which they are bonded, form a 5- to 7-membered cyclic urea, Ar is a group represented by any one of the formulae Ar-1 to Ar-17: 
(wherein Xxe2x80x2 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkoxy group, a C1-C6 alkoxy C1-C6 alkyl group, a NR9R10 group, a CONR9R10 group, a C1-C4 haloalkoxy group, a C2-C6 alkenyloxy group, a C3-C6 cycloalkyloxy group, a C2-C7 acyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsufonyl group, a cyano group, a nitro group or a C1-C4 haloalkyl group, nxe2x80x2 is an integer of from 1 to 3, m is an integer of from 0 to 3, when nxe2x80x2 is an integer of 2 or 3, the plurality of Xxe2x80x2 may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C1-C3 alkylenedioxy group), R7 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C4 haloalkyl group or a C3-C6 cycloalkyl group, and R8 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkylthio group, a C1-C4 haloalkyl group or a C3-C6 cycloalkyl group; and a herbicide containing it as an active ingredient.
Now, definitions of terms used in this specification will be shown below.
The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
The C1-C6 alkyl group means a straight chain or branched chain alkyl group having a carbon number of from 1 to 6, unless otherwise specified, and it may, for example, be a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group or a tert-butyl group.
The C3-C6 cycloalkyl group represents a cycloalkyl group having a carbon number of from 3 to 6, and it may, for example, be a cyclopropyl group, a cyclopentyl group or a cyclohexyl group.
The C2-C6 alkenyl group represents a straight chain or branched chain alkenyl group having a carbon number of from 2 to 6, and it may, for example, be an ethenyl group or a 2-propenyl group.
The C2-C6 alkynyl group represents a straight chain or branched chain alkynyl group having a carbon number of from 2 to 6, and it may, for example, be an ethynyl group or a 2-propynyl group.
The C1-C4 haloalkyl group represents a straight chain or branched chain alkyl group having a carbon number of from 1 to 4, which is substituted by from 1 to 9 same or different halogen atoms, unless otherwise specified, and it may, for example, be a chloromethyl group, a trifluoromethyl group or a tetrafluoroethyl group.
The C1-C6 alkoxy group represents an (alkyl)-O-group wherein the alkyl moiety has the above meaning, and it may, for example, be a methoxy group, an ethoxy group or a propoxy group.
The C2-C6 alkenyloxy group represents an (alkenyl)-O-group wherein the alkenyl moiety has the above meaning, and it may, for example, be an ethenyloxy group or a 2-propenyloxy group.
The C2-C6 alkynyloxy group represents an (alkynyl)-O-group wherein the alkynyl moiety has the above meaning, and it may, for example, be an ethynyloxy group or a 2-propynyloxy group.
The C3-C6 cycloalkyloxy group represents a (cycloalkyl)-O-group wherein the cycloalkyl moiety has the above meaning, and it may, for example, be a cyclopropyloxy group, a cyclopentyloxy group or a cyclohexyloxy group.
The C1-C6 alkoxy C1-C6 alkyl group represents an (alkyl)-O-(alkylene)-group, wherein the alkyl moiety has the above meaning, and it may, for example, be a methoxymethyl group or an ethoxymethyl group.
The C3-C6 cycloalkyl C1-C6 alkyl group represents a (cycloalkyl)-(C1-C6 alkylene) group wherein the cycloalkyl moiety has the above meaning, and it may, for example, be a cyclopropylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group or a cyclohexylethyl group.
The C1-C4 haloalkoxy group represents a (haloalkyl)-O-group wherein the haloalkyl moiety has the above meaning, and it may, for example, be a trifluoromethoxy group or a 2,2,2-trifluoroethoxy group.
The C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group, represent an (alkyl)-S-group, an (alkyl)-SO-group and an (alkyl)-SO2-group, wherein the alkyl moiety has the above meaning, and they may, for example, be a methylthio group, an ethylthio group, a methylsultinyl group, an ethylsulfinyl group, a methylsulfonyl group or an ethylsulfonyl group.
The C2-C6 alkenylthio group, the C2-C6 alkenylsulfinyl group and the C2-C6 alkenylsulfonyl group, represent an (alkenyl)-S-group, an (alkenyl)-SO-group and an (alkenyl)-SO2-group, wherein the alkenyl moiety has the above meaning, and they may, for example, be a propenylthio group, a butenylthio group, a propenylsulfinyl group, a butenylsulfinyl group, a propenylsulfonyl group or a butenylsulfonyl group.
The C2-C6 alkynylthio group, the C2-C6 alkynylsulfinyl group and the C2-C6 alkynylsulfonyl group, represent an (alkynyl)-S-group, an (alkynyl)-SO-group and an (alkynyl)-SO2-group, wherein the alkynyl moiety has the above meaning, and they may, for example, be an ethynylthio group, a 2-propynylthio group, an ethynylsulfinyl group, a 2-propynylsulfinyl group, an ethynylsulfonyl group or a 2-propynylsulfonyl group.
The C3-C6 cycloalkylthio group, the C3-C6 cycloalkylsulfinyl group and the C3-C6 cycloalkylsulfonyl group, represent a (cycloalkyl)-S-group, a (cycloalkyl)-SO-group, and a (cycloalkyl)-SO2-group, wherein the cycloalkyl moiety has the above meaning, and they may, for example, be a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group, a cyclopropylsulfinyl group, a cyclobutylsulfinyl group, a cyclopentylsulfinyl group, a cyclohexylsulfinyl group, a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group or a cyclohexylsulfonyl group.
The C1-C6 alkylthio C1-C6 alkyl group represents an (alkyl)-S-(alkylene) group wherein the alkyl moiety has the above meaning, and it may, for example, be a methylthiomethyl group, an ethylthiomethyl group, a propylthiomethyl group or a methylthioethyl group.
The C2-C7 acyl group represents a C1-C6 alkylcarbonyl group, a C2-C6 alkenylcarbonyl group, a C2-C6 alkynylcarbonyl group, a C3-C6 cycloalkylcarbonyl group or a benzoyl group, and it may, for example, be an acetyl group, a propionyl group, a n-butyryl group, an isobutyryl group, a cyclopropylcarbonyl group or a benzoyl group.
The C1-C6 alkylcarbonyl C1-C6 alkyl group may, for example, be a methylcarbonylmethyl group, an ethylcarbonylmethyl group or a propylcarbonylmethyl group.
The diC1-C6 alkoxy C1-C6 alkyl group may, for example, be a dimethoxymethyl group or a diethoxymethyl group.
The C1-C6 alkoxyimino C1-C6 alkyl group may, for example, be a methoxyiminomethyl group or an ethoxyiminomethyl group.
The hydroxyimino C1-C6 alkyl group may, for example, be a hydroxyiminomethyl group or a hydroxyiminoethyl group.
The cyano C1-C6 alkyl group may, for example, be a cyanomethyl group or a cyanoethyl group.
The C1-C6 hydroxyalkyl group may, for example, be a hydroxymethyl group or a hydroxyethyl group.
The C1-C6 alkoxycarbonyl group may, for example, be a methoxycarbonyl group or an ethoxycarbonyl group.
The C1-C6 alkoxycarbonyl C1-C6 alkyl group may, for example, be a methoxycarbonyl methyl group or an ethoxycarbonyl methyl group.
The carboxyl C1-C6 alkyl group may, for example, be a carboxymethyl group or a carboxyethyl group.
The diC1-C6 alkoxy C1-C6 alkyl group may, for example, be a diethoxymethyl group or a 2-dimethoxyethyl group.
The diC1-C6 alkylamino group is a dialkylamino group wherein the alkylalkyl moiety has the above meaning, and it may, for example, be a dimethylamino group or a diethylamino group.